4-(Chloromethyl)-1-(methylsulfonyl)piperidine → (1R,2S)-2-(4-chlorophenyl)-1'-((1-(methylsulfonyl)piperidin-4-yl)methyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805324Notes

Reaction equation

HRID 1805324 reaction equation
Cl[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH2:5][CH2:4]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[C@:22]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:31])[CH2:21]2)=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C@H:20]2[C@@:22]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:2][CH:3]4[CH2:8][CH2:7][N:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH2:5][CH2:4]4)[C:23]3=[O:31])[CH2:21]2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 283475314-(Chloromethyl)-1-(methylsulfonyl)piperidineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244945(1R,2S)-2-(4-chlorophenyl)-1'-((1-(methylsulfonyl)piperidin-4-yl)methyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 70 starting from 4-chloromethyl-1-methanesulfonyl-piperidine (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C23H25ClN2O35: 444, observed (M+H)+: 445.1 1HNMR (400 MHz, DMSO-d6) δppm 1.23-1.41 (m, 2 H) 1.66-1.78 (m, 2 H) 1.84-1.98 (m, 1 H) 2.02 (dd, J=9.09, 4.80 Hz, 1 H) 2.30 (dd, J=7.71, 4.67 Hz, 1 H) 2.67 (t, J=11.75 Hz, 2 H) 2.83 (s, 3 H) 3.11 (t, J=8.46 Hz, 1 H) 3.56 (d, J=12.13 Hz, 2 H) 3.71 (d, J=7.33 Hz, 2 H) 6.12 (d, J=7.33 Hz, 1 H) 6.66-6.80 (m, 1 H) 7.10-7.20 (m, 2 H) 7.25-7.34 (m, 2 H) 7.34-7.43 (m, 2 H).

Sources & evidence

ORD record
ord-c879878841514909b746f67cb9122e01
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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